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Polymer

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Amino graphene oxide/dopamine modified aramid fibers: Preparation,epoxy nanocomposites and property analysis

Xianyun Gonga, Yuyan Liub,∗, Youshan Wangc, Zhimin Xiec, Qingliang Dongb, Mengyao Dongd,e,Hu Liue, Qian Shaof, Na Lug, Vignesh Murugadossd, Tao Dingh,∗∗, Zhanhu Guod,∗∗∗

a School of Food Engineering, Department of Chemistry, Harbin University, Harbin 150086, ChinabMIIT Key Laboratory of Critical Materials Technology for New Energy Conversion and Storage, School of Chemistry and Chemical Engineering, Harbin Institute ofTechnology, Harbin 150001, ChinacNational Key Laboratory of Science and Technology on Advanced Composites in Special Environment Center for Composite Materials and Structures, Harbin Institute ofTechnology, Harbin 150001, Chinad Integrated Composites Laboratory (ICL), Department of Chemical & Biomolecular Engineering, University of Tennessee, Knoxville, TN 37996, USAe Key Laboratory of Materials Processing and Mold (Zhengzhou University), Ministry of Education; National Engineering Research Center for Advanced Polymer ProcessingTechnology, Zhengzhou University, Zhengzhou, 450002, Henan, Chinaf School of Materials Science and Engineering, Shandong University of Science and Technology, Qingdao 266590, Chinag Lyles School of Civil Engineering, School of Materials Engineering, Birck Nanotechnology Center, Purdue University, West Lafayette, IN 47906, USAh College of Chemistry and Chemical Engineering, Henan University, Kaifeng 475004, China

H I G H L I G H T S

• The self-polymerized polydopamine) (PDA) layer was deposited on aramid fibers.• An efficient route to functionalize aramid fibers based on dopamine chemistry was developed.• With PDA coating and further amino GO grafting, the rougher fiber surface significantly improved the IFSS.

A R T I C L E I N F O

Keywords:PolydopamineAmino graphene oxideInterface properties

A B S T R A C T

Dopamine modified aramid fiber (AF) surface was grafted with amino functionalized graphene oxide to improvethe interfacial adhesive performance. The self-polymerized polydopamine (PDA) coating and subsequent aminoGO grafting on the AF surface attributed to the increase in its surface roughness and surface-active groups. Thefunctional groups, chemical composition and surface topography of unmodified and modified AF was in-vestigated by Fourier transform infrared (FTIR) spectroscopy, X-ray photoelectron spectroscopy (XPS) andScanning electron microscopy (SEM). The interfacial properties were analyzed by measuring interfacial shearstrength (IFSS) of unmodified and modified AF embedded epoxy matrix. Further, the properties were tuned byoptimizing the reaction temperature and concentration of ethylenediamine. The IFSS of AF/epoxy compositeswas increased by 34% after grafting amino graphene oxide.

1. Introduction

With unique properties such as high strength (the single filamentstrength of aramid fiber can reach 3850MPa), good toughness (theimpact strength is 6 times that of graphite fibers), low weight (thedensity of AF is 1.44 g/cm3), low dielectric constant (the dielectricconstant of aramid fiber which contained 58% fibers in the epoxy

composites is 3.3), and good thermal resistance (the thermal decom-position temperature is over 550 °C), aramid fibers (AF) have been apotential reinforcement material for multi-functional composites usedin automobile, aviation, space, bullets, protective garments, electro-magnetic interference shielding, etc [1–7]. However, their poor inter-facial adhesion with the matrix due to the smooth surface and chemicalinertness limits their applications in the composite materials. Therefore,

https://doi.org/10.1016/j.polymer.2019.02.021Received 22 November 2018; Received in revised form 2 February 2019; Accepted 10 February 2019

∗ Corresponding author.∗∗ Corresponding author.∗∗∗ Corresponding author.E-mail addresses: liuyy@hit.edu.cn (Y. Liu), dingtao@henu.edu.cn (T. Ding), zguo10@utk.edu (Z. Guo).

Polymer 168 (2019) 131–137

Available online 12 February 20190032-3861/ © 2019 Elsevier Ltd. All rights reserved.

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many research efforts have been made to improve the interfacialproperties of AF based composites through the modification of AFsurface by plasma treatment, chemical etching, ion sputtering, ultra-sonic treatment, corona discharge and so on [8–10]. Unfortunately,these techniques have drawbacks such as multi-step procedures, highcost, toxic by-products, deterioration of the structure and the propertiesof fibers, thereby restricting the potential performance of the compo-sites [11]. Furthermore, it is worth pointing out that the fiber coating orsizing during composite processing prevents it from breaking andfluffing compared to chemical treatment [12,13].

Very recently, the treatment of fibers using dopamine has attractedresearch interests due to the advantages such as remarkable chemicalproperties, mild reaction conditions, low cost, and easy applicability todifferent materials including non-stick surfaces of various size andshape [14]. Usually, the catechol groups in the dopamine undergo self-oxidative polymerization under the weak alkaline condition to formpolydopamine coating on the fibers [15]. Yang et al. demonstrated thatthe functionalization of graphene with PDA improved their dis-persibility and stress transfer between the polyurethane and the gra-phene [16]. In our earlier work, we modified the surface of AF usingdopamine and investigated the effect of treatment time and dopamineconcentration. It was found that the AF modified with PDA exhibited animproved interfacial shear strength (IFSS). Moreover, the catecholgroups reacted with thiol- or amine-functional groups through Schiffbase reactions or Michael addition under oxidizing conditions [17,18].This facilitated the grafting of functionalized secondary materials ontoPDA, which further improved their functionality and surface reactivity[16,19]. Zhu et al. found that the grafting of graphene oxide on PDAcoated aramid fibers increases their mechanical properties as well asUV-resistance [20]. Sa et al. reported that grafting of epoxy functio-nalized silane improved the adhesion strength of PDA functionalizedmeta-aramid fibers in rubber matrix by 62.5% [21]. In view of these, itis valid to expect the grafting of amino-functionalized graphene oxideon PDA coated aramid fibers to be effective for improving their ad-hesive performance in an epoxy matrix. Herein, amino graphene oxidewas grafted onto the surface of aramid fibers/modified polydopamine-capped utilizing the secondary reaction of active hydrogen in poly-dopamine. The physical properties of the pure AF and modified AF wereinvestigated by (FT-IT) spectroscopy, scanning electron microscopy(SEM) and X-ray photoelectron spectroscopy (XPS). The interfacialadhesive performance of modified AF was analyzed by measuring theIFSS. It is found that the properties of the PDA modified AF varies withvarying the reaction temperature and concentration of ethylenediamineduring grafting of amino graphene oxide.

2. Experimental

2.1. Materials

3,4-dihydroxyphenethylamine hydrochloride (DOPA, 98%), and tris(hydroxymethyl)aminomethane (TRIS, 99%) were purchased from J&KChemicals Ltd. Ethylenediamine (EDA) and graphite powders wereobtained from Aladdin Reagent Corp. (Shanghai, China). KEVLAR49was obtained from J&K Chemicals (DuPont Company, America). Thematrix, epoxy resin (E51) and curing agent, m-Xylylenediamine wereprocured from Shanghai Resin, China. All the chemical reagents andsolvents were of analytical grade and used as received without anyfurther treatment.

2.2. Preparation of amino graphene oxide sample

The graphene oxide (GO) nanosheets were prepared by the modifiedHummer's method [22]. Briefly, 0.1 g GO was dispersed into 100mLdeionized water via ultrasonication for 15min, configured as 1 g/L GOsolution. Then, a certain amount of EDA was added to the GO solutionat 60 °C and later on stirred for 12 h. The solid products were collected

by washing with a copious amount of deionized water and subsequentlydried at 40 °C under vacuum.

2.3. Preparation of amino GO/dopamine modified aramid fibers

Firstly, the as-received AF were extracted with acetone for 24 h toeliminate the commercial sizing and subsequently dried at 40 °C for 6 hunder vacuum. To functionalize the surface of AF, the 2mm long de-sized-AF were immersed in a buffer solution (pH=8.5), and then do-pamine was added. The above mixture was sonicated for 10min andkept under constant stirring for 24 h at room temperature. PDA coatingwas formed on the desized-AF surface by self-oxidative polymerizationof dopamine. The PDA-coated AF was washed and filtered with deio-nized water to remove residual dopamine and PDA. The filtrate wasthen dried at 40 °C for 5 h in vacuum. To obtain amino GO/dopaminemodified aramid fibers, PDA-aramid fibers were added into amino GOsolution to react through amine-catechol adduct formation at 15–50 °Cfor 12–24 h, the amino GO-grafted dopamine modified aramid fiberswere obtained and dried at 50 °C for 24 h under a vacuum.

The mixture of epoxy resin E−51 and m-xylylenediamine in theweight ratio of 100:18.32 was applied on a single aramid fiber to formresin microdroplet. The resin microdroplet was then cured at 60 °C for1 h and at 100 °C for 2 h. The prepared resin microdroplets were used totest the interfacial properties of the modified fibers.

2.4. Characterizations

The molecular elucidation of the GO, amino GO, pure AF and sur-face modified AF was carried out by Fourier transform infrared (FTIR)spectroscopy (Nicolet spectrometer) in the wavenumber range between400 and 4000 cm−1 at a resolution of 4 cm−1. The morphologies of GOand amino GO were investigated using transmission electron micro-scopy (Libra 120). The functional groups and chemical composition ofthe amino GO and surface modified AF surface were characterized by X-ray photoelectron spectroscopy (ESCALAB 220i-XL) with Al-Kα radia-tion. The signals were collected at the 45° of incidence angle. Thesurface topography of the pure AF, PDA-AF and amino GO/PDA-AF wasobserved by using a scanning electron microscope (SEM, Quanta 200FEG).

The micro-debonding test for the prepared resin droplets was car-ried out on an XQ-1 fiber tensile testing machine to investigate theinterfacial properties at a displacement rate of 0.1mm/min. The IFSS(τ) was calculated using Equation (1) [23]:

τ=Fmax/(πDf Le) (1)

where Fmax is maximum pullout force, Df is the diameter of AF, and Le isthe length of AF embedded in the epoxy matrix. The experiment wasrepeated for 30 times and the average value was calculated for eachsample.

3. Results and discussion

3.1. Characterization of GO and amino GO

The preparation process of the Amino GO-PDA-AF/EP is illustratedin Scheme 1. At first, the PDA was attached to the surface of AF via thestrong adhesion of dopamine. This is because the PDA was coated onthe AF surface through an intermolecular cross-linking of 5, 6-dihy-droxyindole resulted from the oxidative conversion of the catecholgroups in dopamine under basic conditions [24–26]. Moreover, thisreaction introduced polar hydroxyl and imine groups to the PDA.Subsequently, the Michael addition reaction between amines and oxi-dized quinone structures resulted in the grafting of amino GO on PDA-AF, which was beneficial to improve the surface activity of the fiber andits interfacial bonding with the epoxy resin.

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The morphologies of the as-obtained graphene oxide (GO) andamino GO are shown in Fig. 1. The cross-sectional view of the atomicforce microscopy (AFM) image demonstrates that the average thicknessof GO is about 1 nm, and a large lateral size exceeds several micrometer(Fig. 1a). It is important to note that a Tyndall effect can be clearlyobserved in the inset of Fig. 1a, indicating its superior dispersity andhydrophilicity. A typical TEM image of GO reveals a thin gauze andwrinkled morphology (Fig. 1b), demonstrating its excellent flexibilityand machinability. In addition, the SEM image of GO also shows similarresults to its TEM (Fig. 1c). Interestingly, the morphology of amino GOis basically the same as that of GO, indicating that the aminationmodification had little effect on the morphology of GO.

The FTIR spectra of GO and amino GO are shown in Fig. 2. It can beseen that the amino GO exhibits the variation in the range between1465 and 1255 cm−1 that is ascribed to the stretching of CeN andbending of NH2 and eNHe groups. In addition, the observed wideningof the peak at 3430 cm−1 represents the combination of OeH and NeHstretching.

Raman spectra of graphite, GO, and amino GO with their char-acteristic G- and D-bands are shown in Fig. 3. The characteristics Gband representing the in-plane vibration of sp2 bonded carbon atoms isobserved for graphite [27–29]. The intensity of the D band associated

with the crystalline grain size and impurity defects of graphite is in-significant because of its crystal symmetries [30]. Interestingly, the GOand amino GO exhibit strong G and D bands. This can be explainedthrough the following reasons. The chemical method adopted for thepreparation of GO involved the exfoliation and introduction of oxygenwithin the graphite layers, which increased the defects of crystals andreduced the number of layers [31,32]. The GO was then reduced withEDA to produce amino GO; however, the reduction reaction caused thefracture of carbon bond and made the crystal sizes smaller [33].

FTIR spectra of amino GO obtained at different temperatures areshown in Fig. 4a. It depicts that the representative peaks of amino GObetween 1465 and 1255 cm−1 and at around 3430 cm−1 (ref. Fig. 2)become intense and wider with the increase in the preparation tem-perature. These results indicate that the amount of amino-functionalgroup grafted on GO increases with increasing the temperature. Fur-ther, the disappearance of the peaks at 1713 and 1070 cm−1 corre-sponding to C]O and CeO, respectively, indicates that the degree ofreduction of GO was increased gradually with increasing temperature[34]. Also, the intensity of their characteristic peaks increases withincreasing the concentration of EDA as seen in Fig. 4b, which indicatesthat increasing the concentration of EDA was helpful to improve thefunctionalization in GO.

The results of the GO XPS spectrum show that the pristine GO was

Scheme 1. Illustration of the manufacturing process of Amino GO-PDA-AF/EP.

Fig. 1. (a) AFM image of GO and the digital photograph of GO solution isshown in the inset. (b) TEM image of GO. SEM images of (c) GO and (d) aminoGO.

Fig. 2. FTIR spectra of graphene, GO and amino GO, respectively.

Fig. 3. Raman spectra of graphene GO and amino GO, respectively.

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comprised of carbon (C) and oxygen (O) species with the oxygen tocarbon signal ratio (O/C) of 0.683. This means that the graphene waswell oxidized. However, the results of the amino GO XPS spectrum inFig. 5 show that the amino GO was composed of carbon (C), oxygen (O)and nitrogen (N) elements. Compared with GO, N element content in-creased from 0 to 7.02%. In addition, the O element content decreasedfrom 40.58% to 24.98%, which indicated that EDA had a certain

reduction effect on the GO. The C1s spectra of amino GO were decon-voluted into five peaks corresponding to CeC at 284.5 eV, CeO at285.5 eV, CeN at 286.2 eV, CeOeC at 286.9 eV, and C]O at 288.1 eV[35]. The results are summarized in Table 1. Compared with the C1sspectra of GO, a CeN peak appeared, the content was 24.49%. TheCeOeC peak became smaller significantly, the content decreased from42.35% to 11.02%. The content of CeO and C]O also slightly declined.These indicate the chemical reaction between EDA and GO. Meanwhile,at the time of reaction, the O atoms, which contained in the CeOeC,disappeared. In addition, the content of CeC increased from 34.71% to53.88% compared with GO, indicating that EDA repaired the damagedCeC sp2 hybrid structure and reduced the GO indeed to some extent.

The N1s spectra of amino GO were fitted into two peaks at 399 and400.5 eV attributed to the eNHe and eNH2e groups, respectively [36].The eNHe was distributed at one end of the combination of EDA andGO, while the NH2 was at the other end of the EDA. It can be clearlyseen from the diagram that the eNH-peak area was obviously largerthan that of the eNH2 peak area. This was because that a part of EDAwas connected between two GO layers, making the content of eNHemore than that of the eNH2e. However, due to excess EDA, there was aconsiderable portion of the eNH2 available, these eNH2 group

Fig. 4. FTIR spectra of (a) amino GO at different preparation temperatures and(b) amino GO at different preparation concentrations of EDA.

Fig. 5. (a) C1s and (b) N1s XPS spectra of amino GO.

Table 1Structure and compositions analysis of C1s Peaks of amino GO.

Chemical bond Peak position Peak area Content (%)

CeC 284.5 63402.77 53.88CeO 285.5 7586.01 6.45CeN 286.2 28819.44 24.49CeOeC 286.9 12972.63 11.02C=O 288.1 4894.75 4.16

Fig. 6. SEM images of the surfaces of (a) pure desized-AF, (b) PDA-AF, (c)amino GO-PDA-AF prepared at 40 °C, and (d) amino GO-PDA-AFs prepared at60 °C.

Table 2Structure and compositions analysis of C1s Peaks of amino GO/dopaminemodified aramid fibers.

Chemical bond Peak position Peak area Content (%)

CeC 284.6 28070.87 45.00CeO 285.6 8312.58 13.33CeN 286.2 13490.92 21.63CeOeC 286.9 5520.67 8.85C=O 288.1 6975.14 11.18

Fig. 7. (a) C1s and (b) N1s XPS spectra of amino GO/dopamine modifiedaramid fibers.

Fig. 8. TGA curves of AF, amined AF, Dopamine/AF and GO.

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provided the active sites of the reaction when the amino GO was graftedto the AF for the next step.

3.2. Research on amino GO/dopamine modified aramid fibers

SEM images depicting the surface morphology of pure desized-AF,PDA-AF and amino GO/PDA-AF prepared at different reaction tem-peratures are shown in Fig. 6. It can be observed that the pure AFpossess clean and smooth surface, and contain some shallow andnarrow micro-grooves along the axial direction (Fig. 6a). After treat-ment with dopamine, the PDA-AF displayed a high roughness surfacewith significant protuberances, indicating the coating of dopamine onthe AF surface by self-oxidative polymerization (Fig. 6b). Fig. 6c and dshows that the amino GO/PDA-AF are covered with flakes of amino GO.It can be clearly seen that the obtained surface of amino GO/PDA-AFbecomes more uneven and much rougher, which is beneficial to im-prove the surface activity of the fiber and its interfacial bonding withthe resini. Moreover, it was also observed that the surface roughness ofPDA-AF and the density of amino GO on their surface increased withthe increase of the reaction temperature from 40 to 60 °C, and the re-sults are consistent with those of the FTIR spectrum analysis. All aboveresults indicate that AF were successfully modified by dopaminetreatment and further grafted with amino GO by reaction with EDA,which gave them the potential to strengthen the epoxy resins.

The surface chemical compositions of amino GO/dopamine mod-ified aramid fibers were further analyzed by using XPS. The results arepresented in Table 2. It can be seen that after grafting, N elementcontent of the modified fibers surface was 9.6%, which was greater thanthat of the amino GO and less than PDA. The content of C element was68.56%, more than 67.37% of PDA. In addition, the content of O ele-ment was 21.84%, less than the content of O in PDA. All these indicatethat the amino GO had been grafted on the AF.

For amino GO/dopamine modified aramid fibers, the C1s spectrawere fitted into five peaks at 284.6 (CeC), 285.6 (CeO), 286.2 (CeN),286.9 (CeO), and 288.1 eV (C]O), respectively (Fig. 7a), consistentwith the previous report [37]. Compared with the C1s spectra of aminoGO, the CeC and CeN bond contents decreased, however, CeO andCeN contents increased, all functional group ratios were close to thevalue of pure PDA. The results indicated that the grafting process in-corporated the nitrogen atoms into the AF surfaces. The amino GO hadbeen successfully grafted on the AF, but it had not completely coveredthe AF, or the thickness was less than the detection depth of XPS.Fig. 7b shows that the N1s spectra of amino GO/dopamine modified AFcan be fitted into only two peaks with BEs at about 399.5 (−NH) and401.4 eV (NH2) [38]. Compared with the N1s fitted results of PDA- AF,the=NeH peak in PDA coating disappeared, and the intensity of theeNH2 peak in the amino GO increased. This indicated that the aminoGO had completely covered the AF, but the thickness of the amino GOcoating has not yet exceeded the detection depth of XPS. The exactcontents of PDA coating on AF and amino GO on the surface modifiedAF can be determined by using thermogravimetric analysis (TGA). Asknown from the calculation (Fig. 8), the content of the PDA coating onAF is 9.2％, and the amino GO on the AF surface modified at tem-perature of 40 °C and 60 °C is 0.7％ and 2.1％, respectively.

The nature of interface/interfacial adhesion is a crucial factor thatdetermines the stress transfer between the reinforcing fibers and thematrix and thereby the mechanical properties of the correspondingcomposites. The IFSS is the parameter that signifies the interfacialproperty of the composites and their values for AF/epoxy composites

prepared at different treatment conditions are presented in Table 3.Evidently, the IFSS of the modified aramid/epoxy composites was sig-nificantly higher than that of the unmodified aramid/epoxy composites.The IFSS of AF/epoxy composites was significantly improved with themodification in AF surface due to the increased surface roughness of AFwith the treatment of dopamine and amino GO. This is mainly becausethat the increase of AF surface roughness can improve the surface ac-tivity of fibers and the interaction with resins. It is important to notethat the IFSS of composites comprising amino GO/PDA-AF is slightlylower than that of the composites comprising the PDA-AFs at a lowerreaction temperature of 40 °C. Although the roughness of the fibersurface increased relatively, the bonding strength between dopamineand aramid fiber was not too high, and the interface between dopamineand aramid fiber was preferred to be separated from the compositematerial when it was pulled away. Interestingly, the IFSS of compositescomprising amino GO/PDA-AF was higher than that of the compositescomprising PDA-AFs at a higher reaction temperature of 60 °C. Theamino GO improved the polarity and surface reactivity of PDA-AF byintroducing the reactive functional groups, thereby improving thewettability and interfacial properties of AF/epoxy interface [39].Moreover, the inherent high specific surface area of amino GO con-tributed to the IFSS by consuming the destructive energy [23].

4. Conclusions

Aramid fibers were modified by self-oxidative polymerization ofdopamine and amino GO grafting. XPS and SEM results confirmed thataramid fibers were coated with PDA and amino GO. The amino GOgrafting improved the surface roughness, polarity and reactivity of thePDA-AF. The amount of amino GO grafting was altered by changing thereaction temperature and concentration of ethylenediamine. At ahigher reaction temperature of 60 °C, amino GO/PDA-AF/epoxy com-posites exhibited IFSS of 35.21MPa, which was 34% higher than that ofpure-AF/epoxy composites (26.31MPa). The improved IFSS demon-strated the satisfactory reinforcing was achieved by modification ofaramid fibers. This study delivers the facile route for the surface mod-ification of high-performance fibers for their potential applications inmultifunctional polymer composites especially with functional nano-particles [40–49] and functional polymers [50–55] for various appli-cations such as electromagnetic interface shielding [56–59], environ-mental remediation [60–64] and sensing [65–69].

Acknowledgments

The authors gratefully acknowledge the financial support by theNational Natural Science Foundation of China (NSFC grant no.51790502), the Harbin University Doctor Foundation by no.HUDF2017101 and Key Laboratory of Functional Inorganic MaterialChemistry (Heilongjiang University), Ministry of Education, China.

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Amino graphene oxide/dopamine modified aramid fibers: Preparation, epoxy nanocomposites and property analysisIntroductionExperimentalMaterialsPreparation of amino graphene oxide samplePreparation of amino GO/dopamine modified aramid fibersCharacterizations

Results and discussionCharacterization of GO and amino GOResearch on amino GO/dopamine modified aramid fibers

ConclusionsAcknowledgmentsReferences